Water → HCID 178436318, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7.88 g of β,β-dibromo-p-(trans-4-pentylcyclohexyl)styrene in 150 ml of absolute tetrahydrofuran was placed at -78° C. in a sulphonation flask under argon gasification and treated within 10 minutes with 63 ml of a 1.2N solution of butyl lithium in hexane. After completion of the addition, the mixture was stirred at -78° C. for a further 1 hour and at -10° C. for 1 hour, then poured into 100 ml of water and extracted three times with 100 ml of petroleum ether each time. The organic phases were washed with 100 ml of water and with 100 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residual crystallizing oil on silica gel with hexane gave 4.13 g (85%) of 1-ethynyl-4-(trans-4-pentylcyclohexyl)benzene as colourless crystals (purity 99.3%); m.p. (C-N) 39.4° C., cl.p. 42.1° C.

Provenance & Evidence